U.S. Pat. No. 4,605,802 is directed to the addition of a haloalkane (carbon tetrachloride) to an alkene (ethylene) in the presence of a phosphite ester complexing agent (such as triethylphosphite) and an iron-containing catalyst material (such as powdered iron or iron chloride) to produce the haloalkane addition product (1,1,1,3-tetrachloropropane). This addition reaction occurs in the absence of solvent. The addition of 1,1,1-trichlorotrifluoroethane to ethylene using an iron/triethylphosphite co-catalyst system in the absence of a solvent was also reported in the Journal of Fluorine Chemistry, 76 (1996) 49-54.
The addition of polyhaloalkanes to 1-octene by an oxidation-reduction addition in the presence of a copper chloride catalyst was reported in Burton et al., Journal of Organic Chemistry (1970), pages 1339 to 1342. A similar type of oxidation-reduction addition was discussed earlier by Asscher et al in an article in the Journal of the Chemical Society (1963) at pages 1887 to 1895. Asscher et al. is directed to the addition of carbon tetrachloride to alkenes in the presence of a copper-containing or iron-containing catalyst. Asscher et al. reported that the use of the metal-containing catalyst effectively minimizes telomerization reactions, thereby producing a greater yield of the 1:1 addition adduct.
Others have generally taught the use of metal-containing catalysts to add haloalkanes across a carbon-carbon multiple bond. For example, T. Asahara et al., in two articles in volume 74 of Kogyo Kagaku Zasshi (1971), at pages 703 to 705 and 2288 to 2290, discuss the reaction of carbon tetrachloride with ethylene in the presence of a phosphite ester complexing agent and metal salts, particularly, iron chloride, to effect telomerization. The reactions proceed to various degrees, producing 1,1,1,3-tetrachloropropane along with relatively large amounts of higher telomers, as follows: EQU CCl.sub.4 +CH.sub.2.dbd.CH.sub.2.fwdarw.CCl.sub.3 (CH.sub.2 --CH.sub.2).sub.n Cl+CCl.sub.2 [(CH.sub.2 --CH.sub.2 ).sub.n Cl].sub.2
wherein n is primarily 1 with significant amounts of n as 2 and 3.
T. Fuchikami et al., an article in Tetrahedron Letters, Vol. 25, No. 3 (1984), at pages 303 to 306, is directed to the use of a transition-metal complex catalyst in the addition of polyfluoroalkyl halides to carbon-carbon multiple bonds.
T. Ishihara et aL, an article in Chemistry Letters (1986), at pages 1895-1896, is directed to the perfluoroalkylation of alkynes with perfluoroalkyl iodides in the presence of a palladium catalyst.
Still others have employed initiators such as amines or amine salts (Brace, J Org. Chem., 44(2) 212-217 (1979)) or arenesulfonate and alkanesulfinate salts (Feiring, J. Org. Chem. 50(18), 3269-3272 (1985)). Other prior art catalysts include Fe(CO)catalyst).sub.5, Mn(CO).sub.10, and RuCl.sub.2.
In these prior art examples, the reaction mechanism is thought to involve radical or radical-type intermediates formed by single electron transfer (SET) processes. The metal component of the catalyst is typically in an electron rich low valence state and transfers a single electron to the haloalkane to initiate the transformation. In other examples, similar addition reactions have been brought about by thermolysis, photolysis, electrolysis, or free radical initiation, for example, using organic peroxides such as benzoyl peroxide. These alternate addition methods all involve radical species as intermediates.
Use of such metal catalysts, however, generally suffer from several drawbacks; e.g., they may be expensive, they may lead to unwanted by-product formation, they may require removal from the final product and they may require special environmental handling and disposal procedures that are nonhazardous to the environment.
An article in the Journal of Fluorine Chemistry, 50 (1990), W. Y. Huang et al., at pages 133-140, is directed to the use of phosphorus derivatives, including triethylphosphite, as catalysts in the presence of excess acetonitrile (i.e., present in an amount that exceeds the total amount of reactants and catalyst). The excess acetonitrile is said to be needed for successful addition of the perfluoroalkyl iodide to the alkene.
However, use of such additives (as in Huang et al) generally suffer from several drawbacks; e.g., the preferred excess component must be determined to maximize process performance, the productivity is lowered by the volume of the excess component carried through the process equipment, the excess component must be dry, and it may require removal in a separate step for recycle or disposal.